CN110642875B - 基于8-甲氧基喹啉构筑的铜配合物及其制备方法和应用 - Google Patents
基于8-甲氧基喹啉构筑的铜配合物及其制备方法和应用 Download PDFInfo
- Publication number
- CN110642875B CN110642875B CN201910837603.XA CN201910837603A CN110642875B CN 110642875 B CN110642875 B CN 110642875B CN 201910837603 A CN201910837603 A CN 201910837603A CN 110642875 B CN110642875 B CN 110642875B
- Authority
- CN
- China
- Prior art keywords
- complex
- methoxyquinoline
- preparation
- scn
- methanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- ZLKGGEBOALGXJZ-UHFFFAOYSA-N 8-methoxyquinoline Chemical compound C1=CN=C2C(OC)=CC=CC2=C1 ZLKGGEBOALGXJZ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 150000004699 copper complex Chemical class 0.000 title claims description 14
- 239000010949 copper Substances 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 8
- SRXOCFMDUSFFAK-UHFFFAOYSA-N dimethyl peroxide Chemical compound COOC SRXOCFMDUSFFAK-UHFFFAOYSA-N 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 56
- 239000013078 crystal Substances 0.000 claims description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 22
- 239000012046 mixed solvent Substances 0.000 claims description 15
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical group [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 230000000259 anti-tumor effect Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229940116357 potassium thiocyanate Drugs 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 abstract description 8
- 210000004881 tumor cell Anatomy 0.000 abstract description 6
- 238000002474 experimental method Methods 0.000 abstract description 5
- 230000008859 change Effects 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 210000004027 cell Anatomy 0.000 description 22
- 239000000047 product Substances 0.000 description 17
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 16
- 239000012634 fragment Substances 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 15
- 239000003446 ligand Substances 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000013467 fragmentation Methods 0.000 description 5
- 238000006062 fragmentation reaction Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 230000001028 anti-proliverative effect Effects 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003775 Density Functional Theory Methods 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002050 diffraction method Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- PYHGMRPBEQFDEC-UHFFFAOYSA-N 2-(2-hydroxyethyl)benzonitrile Chemical compound OCCC1=CC=CC=C1C#N PYHGMRPBEQFDEC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 229910002480 Cu-O Inorganic materials 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 238000000134 MTT assay Methods 0.000 description 1
- 231100000002 MTT assay Toxicity 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical group O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
- NHELIHXBJRANPL-UHFFFAOYSA-L copper;diperchlorate;hexahydrate Chemical group O.O.O.O.O.O.[Cu+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O NHELIHXBJRANPL-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- -1 lanthanide metals Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- UTCARTSNNKGRTD-UHFFFAOYSA-N terbium(3+);trinitrate;hexahydrate Chemical group O.O.O.O.O.O.[Tb+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O UTCARTSNNKGRTD-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910837603.XA CN110642875B (zh) | 2019-09-05 | 2019-09-05 | 基于8-甲氧基喹啉构筑的铜配合物及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910837603.XA CN110642875B (zh) | 2019-09-05 | 2019-09-05 | 基于8-甲氧基喹啉构筑的铜配合物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110642875A CN110642875A (zh) | 2020-01-03 |
CN110642875B true CN110642875B (zh) | 2021-02-09 |
Family
ID=69010061
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910837603.XA Active CN110642875B (zh) | 2019-09-05 | 2019-09-05 | 基于8-甲氧基喹啉构筑的铜配合物及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110642875B (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006099685A1 (en) * | 2005-03-24 | 2006-09-28 | Medical Therapies Limited | Method for the prophylaxis or treatment of carcinomas |
CN107098921A (zh) * | 2017-05-19 | 2017-08-29 | 广西师范大学 | 以8‑羟基喹啉酰腙衍生物为配体构筑的镝配合物及其合成方法和应用 |
CN107501303A (zh) * | 2017-08-04 | 2017-12-22 | 广西师范大学 | 一种布洛芬与喹啉‑8‑甲醛席夫碱构筑的铜(ii)配合物及其合成方法和应用 |
-
2019
- 2019-09-05 CN CN201910837603.XA patent/CN110642875B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006099685A1 (en) * | 2005-03-24 | 2006-09-28 | Medical Therapies Limited | Method for the prophylaxis or treatment of carcinomas |
CN107098921A (zh) * | 2017-05-19 | 2017-08-29 | 广西师范大学 | 以8‑羟基喹啉酰腙衍生物为配体构筑的镝配合物及其合成方法和应用 |
CN107501303A (zh) * | 2017-08-04 | 2017-12-22 | 广西师范大学 | 一种布洛芬与喹啉‑8‑甲醛席夫碱构筑的铜(ii)配合物及其合成方法和应用 |
Non-Patent Citations (1)
Title |
---|
Two hydrazone copper(II) complexes: synthesis, crystal structure, cytotoxicity, and action mechanism;Kun Hu等;《RSC Advances》;20160405;第6卷;第36077-36084页 * |
Also Published As
Publication number | Publication date |
---|---|
CN110642875A (zh) | 2020-01-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Ji et al. | Copper (I) halide clusters based upon ferrocenylchalcogenoether ligands: donors, halides and semi-rigidity effects on the geometry and catalytic activity | |
Mahmoudkhani et al. | Layered calcium phenylphosphonate: Synthesis and properties | |
CN110642875B (zh) | 基于8-甲氧基喹啉构筑的铜配合物及其制备方法和应用 | |
CN107827914B (zh) | 一种铜席夫碱配合物及其制备方法和应用 | |
CN110330533B (zh) | 2-甲基-8-羟基喹啉与托酚酮混配铂配合物及其制备方法和应用 | |
Thakuria et al. | CuO micro plates from a 3D metallo-organic framework (MOF) of a binary copper (II) complex of N, N-bis (2-hydroxyethyl) glycine | |
Litvinova et al. | Coordination polymers based on rhenium octahedral chalcocyanide cluster [Re6Se8 (CN) 6] 4–and lanthanide ions solvated with dimethylformamide | |
CN113735781B (zh) | 一种铜配合物及其制备方法和应用 | |
Liu et al. | Synthesis and Anticancer Properties of Rare Earth Substituted Tungstophosphoric Polyoxometalate Containing 5‐Fluorouracil | |
Quiroga-Gonzalez et al. | Zero-and one-dimensional thioindates synthesized under solvothermal conditions yielding α-In2S3, β-In2S3 or MgIn2S4 as thermal decomposition products | |
Girma et al. | Coordination chemistry of acrylamide 3: Synthesis, crystal structure and IR spectroscopic properties of dichloro-tetrakis (O–acrylamide) copper (II),[Cu (O–OC (NH2) CHCH2) 4Cl2] | |
Brahma et al. | New metal-organic precursors for MOCVD applications: Synthesis, characterization, crystal structure and thermal properties of mixed-ligand Mg (II) complexes | |
Schmitz et al. | A planar decanuclear cobalt (II) coordination cluster | |
Grupce et al. | Monoaquabis (2, 2′-bipyridine) saccharinatozinc (II) Saccharinate. 1. Structural Study by Single Crystal X-Ray Diffraction, FTIR, and DS Calorimetry | |
Park et al. | Synthesis and crystal structures of S2O2-donor macrocycles and their silver (I) metallopolymers | |
Anjali et al. | Syntheses, characterization and thermal properties of [M (Spy) 2 (SpyH) 2](M= Cd and Hg; Spy−= pyridine-4-thiolate; SpyH= pyridinium-4-thiolate)) and [M (SpyH) 4](ClO4) 2 (M= Zn, Cd and Hg | |
Kudayarova et al. | Synthesis and structure of 3, 5-diamino-1, 2, 4-triazolium tetrachloro-gallate | |
CN110950913B (zh) | 以9-醛基-10-嘧蒽腙为配体的离子型金属配合物及其合成方法和应用 | |
Ivanova et al. | Coordination ability of silver (I) with antimycins and actinomycins–Properties of the T-shaped chromophores | |
CN109320534B (zh) | 氧化荷苞牡丹碱稀土配合物及其合成方法和应用 | |
Bilge et al. | Complexes of Ni (II) and Pd (II) ions with 15-and 17-membered macrocycles containing O2N2-and O2N3-donors and the crystal structures of Ni (II) and Pd (II) complexes of 2, 5-dioxa-13, 16, 19-triazatricyclo [19.4. 0.06, 11]-pentacosa-6, 8, 10, 21, 23, 25 (1)-hexaene | |
CN110256504B (zh) | 环庚三烯酚酮与8-羟基喹啉混配铂配合物及其制备方法和应用 | |
CN109988185A (zh) | 具有较强抗肿瘤选择性的铂镝杂金属化合物及其制备方法 | |
CN110357926B (zh) | 环庚三烯酚酮与邻菲啰啉混配锰配合物及其制备方法和应用 | |
Olczak-Kobza | Synthesis and thermal analysis of cadmium complexes of imidazole and its derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230705 Address after: No.500-432, Hangshu Avenue, Dongsheng Street, Shuangliu District, Chengdu, 610000, Sichuan Patentee after: Chengdu Chongyuniao Environmental Protection Technology Co.,Ltd. Address before: 541004 No. 15 Yucai Road, Qixing District, Guilin, the Guangxi Zhuang Autonomous Region Patentee before: Guangxi Normal University |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20231201 Address after: 510000, No. 106, Fengze East Road, Nansha District, Guangzhou City, Guangdong Province (self-compiled building 1) X1301-E011212 (cluster registration) (JM) Patentee after: Guangzhou Specialized Enterprise Information Technology Co.,Ltd. Address before: No.500-432, Hangshu Avenue, Dongsheng Street, Shuangliu District, Chengdu, 610000, Sichuan Patentee before: Chengdu Chongyuniao Environmental Protection Technology Co.,Ltd. |
|
TR01 | Transfer of patent right |